http://www.JewishWorldReview.com | I received an e-mail the other day from a friend who thanked me for my advice. Having long ago lost touch with him, I barely remembered the incident to which he referred.

Years ago, he and I spent an afternoon on a boat on Lake Erie, next to Cleveland. He began complaining about his job, and after quietly listening for several minutes, I said, "And what do you intend to do about it?" He stared back, somewhat blankly. I repeated, "What do you intend to do about it?"

He told me that it never occurred to him that he had the option of simply reassessing his situation, perhaps quitting his job altogether and starting something different. He told me he'd once thought about leaving and starting a business, but, after all, that entailed risk and he feared disaster.

I told him, "The worst disaster is to look back and say, 'What if?'" He asked me why I felt so strongly about taking chances, and I told him a story.

When I practiced law in the late '70s, my law firm offered the chance to spend the summer working for the United Way as a "loan executive." As an L.E., I learned to give a speech about the organization -- the percentage of the donated dollar that gets down to the beneficiaries, the efficiency of the organization, etc.

I agreed to participate in the program upon one condition -- that my United Way supervisor assign me to the business division. As an L.E. for the business section, my job required me to meet first with CEOs of medium and large corporations. The CEO and I would then get into a car and drive to a non-United Way supporting colleague of the CEO's, at which time I would make my pitch to the nonparticipating CEO's workforce. I chose the business sector so that I could have some one-on-one face time -- usually an hour each way in the car -- with these successful CEOs. I asked them how they got started. Why they went into business. What mistakes they made along the way. And, most important, I asked, if you were starting out today, knowing what you know now, what advice would you have given yourself?

Mind you, each of these CEOs ran successful companies with gross revenues from 25 million to over 100 million in 1970s dollars. Nearly all started out in humble circumstances, without inherited wealth. They started a business, with some, at first, failing a couple of times. One business distributed shoes. Another shipped goods. Another manufactured car antennae. These 50-something CEOs were, in my mind, huge risk-takers.

But when I asked what advice they would've given themselves as youthful entrepreneurs, all said the same thing: "Take more risks."

These men told me about opportunities they had walked away from, not because they presented poor opportunities, but because they feared taking on too much. Again, many of these entrepreneurs started businesses and failed. But they considered the "failures" learning experiences that hardened and wizened them for future opportunities. All regretted, however, that they failed to stick their necks out even more. "Larry, don't be afraid to fail," they all told me with more or less those same words.

Though I obtained my law degree, I expected my career path to lead elsewhere. I practiced law for about two-and-a-half years and then started a small business that I ran, with reasonable success, for 15 years. I then turned my energies to political and social commentary, and moved into television and radio. I always wanted to write, and managed, in books and columns, to pull it off.

I just turned 55 years old. I consider my life blessed. My mom recently died, but lived to a robust, hearty 81 years. My dad, at 91 years old, still lives in the house where I grew up. We talk every day. I'm lucky that I get to see him frequently, and he remains in excellent health. He takes pride in being "independent and self-supporting." That's his way of declining my numerous offers to come and live with me. He still makes me laugh.

I feel that I perform meaningful work, and I embrace my faith and cherish my family and friends.

But . . . I wish I had taken more risk.

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